Fleming Key Vacation Packages 2026 from $634

Fleming Key flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Barcelona Studios Guesthouse

South Beach

Save 100% on your flight

$634

per person

Aug 13 - Aug 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

Free WiFi in public areas, a garden, and a picnic area are available at this guesthouse. Express check-out and a virtual front desk are also provided.

Casablanca Miami Beach

North Beach

Save 100% on your flight

$1,005

per person

Aug 13 - Aug 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

An outdoor pool, valet parking, and laundry facilities are featured at this aparthotel. A grocery/convenience store, a communal living room, and express check-out are also on offer.

Tower at The Boca Raton

Save 100% on your flight

$1,781

per person

Aug 16 - Aug 21

found 6 hours ago

Roundtrip flight included

Detroit (DTW) to Miami (MIA)

This luxury resort features a golf course, free water park access, and a full-service spa. There's fun for all ages with a lazy river and a children's club, and supervised childcare is an added bonus. Enjoy a meal in one of the 10 restaurants and freebies like WiFi in public areas and a beach shuttle.

Yacht Club at The Boca Raton (Adults-only)

East Boca Raton

Save 100% on your flight

$1,589

per person

Aug 16 - Aug 21

found 6 hours ago

Roundtrip flight included

Detroit (DTW) to Miami (MIA)

This Mediterranean resort features a golf course, free water park access, and a full-service spa. Enjoy a meal in one of the 10 restaurants and free perks like continental breakfast and a beach shuttle. Relax with a drink at one of the 3 beach bars and enjoy the 4 outdoor pools and gym.

Lux Brickell by Palermo Home

Brickell

Save 100% on your flight

$649

per person

Sep 17 - Sep 22

found 14 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

An outdoor pool is featured at this apartment, along with valet parking. WiFi in public areas is free. A garden is provided and the front desk is staffed around-the-clock.

Top Fleming Key hotels deals

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$202 nightly

$228 total

Jul 15 - Jul 16

Total with taxes and fees

This smoke-free hotel features a private beach, a marina, and 2 restaurants. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and an area shuttle.

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$218 nightly

$245 total

Aug 11 - Aug 12

Total with taxes and fees

This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

$171 nightly

$192 total

Aug 12 - Aug 13

Total with taxes and fees

This hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and an area shuttle.

Hyatt Centric Key West Resort and Spa

601 Front St Key West FL

Free Cancellation

Reserve now, pay when you stay

$261 nightly

$294 total

Aug 11 - Aug 12

Total with taxes and fees

This smoke-free resort features a full-service spa, a marina, and a restaurant. Enjoy the outdoor pool and perks like free WiFi. Enjoy the 24-hour gym and unwind at the bar/lounge and poolside bar.

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard Key West FL

$238 nightly

$268 total

Aug 11 - Aug 12

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's a 24-hour gym on site, and a 24-hour front desk and a terrace are also provided.

Pier House Resort & Spa

1 Duval St Key West FL

Free Cancellation

Reserve now, pay when you stay

$382 nightly

$429 total

Aug 13 - Aug 14

Total with taxes and fees

This smoke-free resort features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the 2 conference rooms, business center, and express check-in.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much are vacation packages to Fleming Key?

Vacation packages, which include flights and hotels in Fleming Key, start from just $634. Make your travel dreams a reality and secure your vacation with Travelocity today.

Where can I get the best vacation package deals for Fleming Key?

One word — Travelocity. With no less than 400 partner airlines and 1,000,000 properties across the globe, it's a breeze to craft a Fleming Key package deal that fits your budget.

Why should I book my Fleming Key vacation bundle via Travelocity?

Nothing beats the feeling of knowing you've bagged the best price available — that's our Price Match Guarantee. Add to that our enormous range of destinations and 24/7 team of customer service professionals and you've got the formula for an unforgettable vacation.

Can I save on my Fleming Key car rental if I bundle it with my hotel or flight?

Certainly — and if you also add a tour to your Fleming Key vacation package, you'll pick up even greater savings. With an affordable package from Travelocity, you can find things to do around the region that interest you. Then, jump in your rental car and work your way through the list. Zoo Miami is one terrific sight to put on your itinerary. It's 110 mi from Fleming Key.

What is the best time of year to go to Fleming Key?

If you really want to wander wisely, is one of the best times to do it. That's when hotel rates are at their cheapest. In contrast, prices are at their highest around . January, February and March are the most popular times to vacation in Fleming Key, so expect long queues for famous attractions. Rather avoid the busy season? You'll find fewer crowds during August, September and October.